Method of finishing fibrous material



Patented Sept. 29, '1936 METHOD OF FINISHING FIBROUS MATERIAL Walther Schrauth, Berlin-Dahlem, Germany, as-

signor, by mesne assignments, to E. I. du Pont de Nemours & Company, Wilmington, Del., a

' corporation of Delaware No Drawing. Application November 30, 1934, Serial No. 755,418. In Germany October 7, 1930 8 Claims. (01. 91-68) The present inventionrelates to the treatment of fibrous material and has for an object to provide an improved softening, smoothing and revivifying treatment for natural and artificial fichloride'into the corresponding fatty acid chlorides which are purified by means of vacuum distillation. They are then caused to re-act with the appropriate quantity of borneol correspondespecially the latter.

brous materials including yarns, fabrics, leather ing to their saponification number. The several and artificial leather. terpene alcohol esters of palmkernel oil fatty It has been discovered in accordance with the acids, of cocoanut oil fatty acids or of other fatty present invention that a particularly eiiective acids can be obtained in a similar manner and treatment for natural and artificial fibrous mateare suitable for use for the purposes of this inrial is provided when these materials are treated vention. 10 with softening and smoothing baths comprising Terpene alcohol esters of the naphthenic acids as principal active ingredients cyclic alcohol esters may be produced as follows:-To one molecular of high molecular fatty acids, or of cyclic acids proportion of naphthenic acid is added a little such as the monoand poly-nuclear aromatic, more than one molecular proportion of thionyl hydro-cyclic, or hetero-cyclic mono-carboxylic chloride and the whole is warmed in a water acids. Such .esters are for example the vcyclobath to about 40 0., after which, .after distilling hexyl ester of palmitic acid, the methyl-cyclooff the excess thionyl chloride, naphthenic acid hexyl ester of oleic acid, the borneyl or fenchyl chloride remains. This is then treated in the ester of cocoanut-oilor palmkernel-oil-fatty usual manner at a temperature of about 80 -100 g acid, the terpineol ester of naphthenic acid, the C. with the alcohol, terpineol or other terpene cyclohexyl ester of abietic acid, the cyclohexyl alcohol, to form the ester. v or borneyl ester of the montanic acid. The cyclo-hexyl ester of abietic acid may be The alcohols used in the preparation of these prepared by heating one molecular proportion esters may be any of the cyclic alcohols including of abietic acid ethyl or 'butyl ester with one molecthe terpene alcohols and their alkyl derivatives, ular proportion of cyclohexyl alcohol in the pres- 25 as, for example, terpineol or rfenchyl alcohol, the ence of molecular proportion'of sodium metal monoand poly-nuclear aromatic or hydrocyclic until ethylor butyl alcohol no more distils. The alcohols, for example, benzyl-,- cyclohexyl-, residue left after distillation is washed with Water methyl cyclohexyl, phenyl ethyl-, cinnamyl-, until neutral reaction occurs and then distilled in etc.- alcohols, the hydro-cyclic alcohols includvacuo. 30

mg especially the naphthenic alcohols. The acids The material to be finished may conveniently used may include the aliphatic saturated, 'unbe treated with dispersions of the selected esters saturated and hydroxy acids containing 6 to 30 in organic solvents, for example, benzene, turcarbon atoms in the molecule, the naphthenic pentine, pyridine, hydrogenated naphthalene or acids, the monoand poly-nuclear'arom'atic acids, inemulsions or in any softening, smoothing, reas example, benzoic, phenyl-acetic, toluic, and vivifying or other treating'material. For the forcinnamic acids and the resinic acids as abietic mation of desired emulsions any suitable disperacid and the like. Of the aliphatic acids those sion agent such as sulfonated oils, sulfonated containing 6 to 12 carbon atoms are preferred in alcohols, ester salts or xanthogenates of higher 40 general but for some special uses those having molecular alcohols or even soap may be used. 4.0

12 to 18 carbon atoms produce very satisfactory The solvents or the non-solvents with or with-' results. out such agents as the sulfonated oils or sul- The several esters may be prepared in accord-' ionated alcohols constitute efiective dispersion ance with processes which are known and deagents inert to the material to be treated in that scribed in the literature. For example, they can they'have no detrimental action on the fibrous 45 be prepared by the direct re-action of the acids material, leatherand the like. After treatment with the alcohols by heating a mixture thereof and removal of the solvents or other dispersion in the presence of sulfuric acid or hydrochloric agents the materials treated exhibit an extra acid. They can be prepared by re-acting a salt ordinary smoothness and finish. The proposed of the acid such as the sodium or potassium salt esters are odorless or substantially so and impart with a chloride of the alcohol. no unpleasant odor but they impart desirable For example, to produce "the borneol esters of water repellant properties to the materials treat 1 cocoanut oil fatty acids, the fatty acid mixture ed. These properties are desirable and imporobtainable by saponifying cocoanut oil iscon-- tant for wool, cotton, silk and artificial silk,

verted in the usual way with phosphorus penta- 55 These same esters are useful as ingredients in impregnation or treating agents of various kinds such, for example, as additions to shoe polishes and polishing waxes to be used where a smoothness and softness of the treated material is de-' sirable.

Furthermore these esters are valuable as ingredients of pigments and of preparations for the surface treatment of metals (lubricating agents) partly because they are entirely neutral and nearly non-saponifiable.

A very high grade revivifying agent maybe obtained by combining 20 parts by weight of the methylcyclohexylpalmitic ester with 80 parts of a highly sulfonated Turkey red oil.

A polishing wax may be produced by substituting in the usual compositions cyclohexyl or borneyl ester of the montanic'acid for one part of the wax constituents, and. a metal cleaning agent may be compounded by mixing 10 parts of the ester of terpineol with-naphthenic acid with 50 parts siliceous chalk and 40 parts of a volatile solvent.

These esters are also useful as plasticizing agents in elastic non-brittle lacquer coatings and films and plastic masses made from cellulose esters or ethers and add durability and mechanical resistance as well as flexibility. It may be noted that by using the new agents cellulose ester and ether lacquers can be produced which contain in addition to the usual materials also a certain amount of caoutchouc and that thereby the strength and flexibility and the extensibility may be considerably increased.

For example, parts of nitrocellulose are disi solved in 29 parts of butylacetate and 11 parts of ethyl alcohol and mixed together with 4 parts of the ester formed by heating methylcyclohexa- 1101 with palmitic acid. After pouring and evaporating a soft and homogeneous film is obtained.

In the preceding example the nitrocellulose might be replaced by other esters of cellulose, if

by means of a proper combination of the solvent- .components a premature separation in flakes is avoided. Y The methylcyclohexylpalmitate can be replaced by the other above-mentioned esters, for example, by terpineol ester of the fatty'acids as obtained from cocoanut oil or palmkernel oil, or the borneyl ester of naphthenic acid.

Plastic masses, possessing the properties of the basic-substances, i. e. the softness of the nitrocellulose products and the plasticizing properties of the caoutchouc are produced according to the following prescription:

Parts Nitrate of cellulose 3 Hevea crepe 1 Butylacetate 30 Cyclohexanone 15 Cyclohexylacetate 5 One of the above mentioned esters '7 The mixture is dissolved by heating up to 70 homogeneously and afterwards dried in a suitable manner.-

Some of the several esters mentioned have among themselves special characteristics rendering them particularly suitable for certain uses.

For treating fibrous material a mixture is suitable consisting'of 80 parts of the methyl cycloof methyl cyclohexyl alcohol.

hexyl ester of oleic acid and 20 parts .of soap containing 60 parts of oleateof potash and 40 parts An aqueous emulsion containing 5 percent of the above mixture is a particularly effective revivifying bathfor fibrous materials such as rayon or artificial silk.

A leather varnish which is suitable for the manufacture oi. artificial leather is produced according to the following prescription:

i Parts Nitrate of cellulose 7 Butyl acetate 30 Amy] acetate 15 Toluene- 30 Acetanilide 1 Methylcyclohexyl ester of palmitic acid 3 'Di-methylcyclohexyl-ester of methyl-adipic arid A textile fabric such as shirting is in the usual manner spread over several times with the above mixture. It is possible to employ a large quantity of the mixture, because it is not adhering and furnishes a very smooth product.

The foregoing application 'is a continuation in part of applicants co-pending application Serial No. 567,309 filed October 6th, 1931.

What I claim is:

1. The method of treatment of fibrous material of abietic acid.

3. The method of treatment of fibrous material or metal and wood surfaces which consists in applying thereto, treating material containing as a principal ingredient the borneyl ester of cocoanut oil-fatty acid.

4. The method of treatment of fibrous material or metal and wood surfaces which consists in applying thereto, treating material containing as a principal ingredient the terpineol ester of naphthenic acid. 5. A composition for treating fibrous materi which consists of an ester selected from the group consisting of the borneyl and fenchyl esters of cocoanut-oil and palmkernel oil fatty acid,

' the terpineol ester of naphthenic'acid, the cyclohexyl ester of abietic acid, and'the cyclohexyl and borneyl esters of montanic acid.

6. A composition for treating fibrous material comprising as its principal active ingredient the methyl cyclohexyl ester of abietic acid.

7. A composition for treating fibrous material comprising as its principal active ingredient the borneyl ester of cocoanut oil fatty acid. 1 8. A composition for treating fibrous material comprising asits principal active ingredient the terpineol ester of naphthenic acid.

WALTHER scrmao'rir. 

